NP-MRD: Showing NP-Card for 5,7-dihydroxy-3',4',5'-trimethoxyflavone (NP0024993)

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Record Information

Version

2.0

Created at

2021-06-19 17:13:50 UTC

Updated at

2021-06-29 23:49:39 UTC

NP-MRD ID

NP0024993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-3',4',5'-trimethoxyflavone

Provided By

JEOL Database JEOL Logo

Description

5,7-Dihydroxy-3',4',5'-trimethoxyflavone, also known as tricetin 3',4',5'-trimethyl ether or dimethyl benzoylphosphonate, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, 5,7-dihydroxy-3',4',5'-trimethoxyflavone is considered to be a flavonoid. 5,7-dihydroxy-3',4',5'-trimethoxyflavone is found in Chrysanthemum morifolium, Haplopteris anguste-elongata, Lycopodium japonicum and Teucrium heterophyllum. 5,7-dihydroxy-3',4',5'-trimethoxyflavone was first documented in 2005 (PMID: 16124757). Based on a literature review a small amount of articles have been published on 5,7-Dihydroxy-3',4',5'-trimethoxyflavone (PMID: 25114960) (PMID: 21061216).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119133D          

 41 43  0  0  0  0            999 V2000
    5.9276    1.4120    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055    1.0498   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5163    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.9897   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.5333    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.0302   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.3322   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.7623   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    3.9391   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    1.7211   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    2.0230   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    3.2947   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.0102   -2.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3022   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974   -1.3270   -2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -0.6141   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    0.4041   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    0.0421   -0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.4329    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.9393    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8855    2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -2.3088    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.4769    1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.9913    1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -2.1666    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    2.2471   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293    0.5841    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.7485    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    1.7224   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007    3.1062   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    3.9037   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432    1.2620   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0281   -0.9697   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -1.6444   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.7803    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6943   -3.0200    3.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.8286    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -1.4679    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.9598    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.9455   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2533   -2.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
  5 19  1  0  0  0  0
 14 16  1  0  0  0  0
 19 20  2  0  0  0  0
 13 11  1  0  0  0  0
 20 23  1  0  0  0  0
 11 10  2  0  0  0  0
 23  3  2  0  0  0  0
 17 16  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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 17 18  1  0  0  0  0
 23 24  1  0  0  0  0
 10  8  1  0  0  0  0
 24 25  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  2  0  0  0  0
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  3  2  1  0  0  0  0
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  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 22 36  1  0  0  0  0
 22 37  1  0  0  0  0
 22 38  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.9276    1.4120    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055    1.0498   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5163    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.9897   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.5333    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.0302   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.3322   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.7623   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    3.9391   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    1.7211   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    2.0230   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    3.2947   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.0102   -2.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3022   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974   -1.3270   -2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -0.6141   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    0.4041   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    0.0421   -0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.4329    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.9393    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8855    2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -2.3088    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.4769    1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.9913    1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -2.1666    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    2.2471   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293    0.5841    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.7485    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    1.7224   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007    3.1062   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    3.9037   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432    1.2620   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0281   -0.9697   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -1.6444   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.7803    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6943   -3.0200    3.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.8286    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -1.4679    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.9598    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.9455   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2533   -2.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
  5 19  1  0
 14 16  1  0
 19 20  2  0
 13 11  1  0
 20 23  1  0
 11 10  2  0
 23  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
  6  5  1  0
 17 18  1  0
 23 24  1  0
 10  8  1  0
 24 25  1  0
  8  7  1  0
 14 15  1  0
  7  6  2  0
 11 12  1  0
  6 18  1  0
  3  2  1  0
 17 10  1  0
 20 21  1  0
  8  9  2  0
  2  1  1  0
 21 22  1  0
 13 32  1  0
 16 34  1  0
  7 30  1  0
 19 35  1  0
  4 29  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
 15 33  1  0
 12 31  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END


  Mrv1652306192119133D          

 41 43  0  0  0  0            999 V2000
    5.9276    1.4120    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055    1.0498   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5163    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.9897   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.5333    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.0302   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.3322   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.7623   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    3.9391   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    1.7211   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    2.0230   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    3.2947   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.0102   -2.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3022   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974   -1.3270   -2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -0.6141   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    0.4041   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    0.0421   -0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.4329    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.9393    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8855    2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -2.3088    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.4769    1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.9913    1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -2.1666    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    2.2471   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293    0.5841    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.7485    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    1.7224   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007    3.1062   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    3.9037   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432    1.2620   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0281   -0.9697   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -1.6444   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.7803    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6943   -3.0200    3.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.8286    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -1.4679    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.9598    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.9455   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2533   -2.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
  5 19  1  0  0  0  0
 14 16  1  0  0  0  0
 19 20  2  0  0  0  0
 13 11  1  0  0  0  0
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 11 10  2  0  0  0  0
 23  3  2  0  0  0  0
 17 16  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
 23 24  1  0  0  0  0
 10  8  1  0  0  0  0
 24 25  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  2  0  0  0  0
 11 12  1  0  0  0  0
  6 18  1  0  0  0  0
  3  2  1  0  0  0  0
 17 10  1  0  0  0  0
 20 21  1  0  0  0  0
  8  9  2  0  0  0  0
  2  1  1  0  0  0  0
 21 22  1  0  0  0  0
 13 32  1  0  0  0  0
 16 34  1  0  0  0  0
  7 30  1  0  0  0  0
 19 35  1  0  0  0  0
  4 29  1  0  0  0  0
 25 39  1  0  0  0  0
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 15 33  1  0  0  0  0
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 22 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C([H])=C(OC2=C1[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-22-15-4-9(5-16(23-2)18(15)24-3)13-8-12(21)17-11(20)6-10(19)7-14(17)25-13/h4-8,19-20H,1-3H3

> <INCHI_KEY>
CPCPHNWWTJLXKQ-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.81405084051154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.180376670924554

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.577707939019336

> <JCHEM_PKA_STRONGEST_BASIC>
-4.403286650446185

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3',4',5'-O-trimethyltricetin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.9276    1.4120    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055    1.0498   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5163    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.9897   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.5333    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.0302   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.3322   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.7623   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    3.9391   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    1.7211   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    2.0230   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    3.2947   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.0102   -2.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3022   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974   -1.3270   -2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -0.6141   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    0.4041   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    0.0421   -0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.4329    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.9393    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8855    2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -2.3088    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.4769    1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.9913    1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -2.1666    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    2.2471   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293    0.5841    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.7485    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    1.7224   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007    3.1062   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    3.9037   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432    1.2620   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0281   -0.9697   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -1.6444   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.7803    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6943   -3.0200    3.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.8286    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -1.4679    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.9598    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.9455   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2533   -2.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
  5 19  1  0
 14 16  1  0
 19 20  2  0
 13 11  1  0
 20 23  1  0
 11 10  2  0
 23  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
  6  5  1  0
 17 18  1  0
 23 24  1  0
 10  8  1  0
 24 25  1  0
  8  7  1  0
 14 15  1  0
  7  6  2  0
 11 12  1  0
  6 18  1  0
  3  2  1  0
 17 10  1  0
 20 21  1  0
  8  9  2  0
  2  1  1  0
 21 22  1  0
 13 32  1  0
 16 34  1  0
  7 30  1  0
 19 35  1  0
  4 29  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
 15 33  1  0
 12 31  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       5.928   1.412   0.399  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.906   1.050  -0.528  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.783   0.516   0.050  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.575   0.990  -0.468  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.348   0.533   0.033  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.066   1.030  -0.505  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.137   2.332  -0.755  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.441   2.762  -1.280  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.679   3.939  -1.528  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.451   1.721  -1.495  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.724   2.023  -1.993  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.116   3.295  -2.313  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.661   1.010  -2.184  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.314  -0.302  -1.874  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.197  -1.327  -2.043  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.051  -0.614  -1.377  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.117   0.404  -1.188  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.889   0.042  -0.695  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.351  -0.433   1.054  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.551  -0.939   1.566  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.641  -1.886   2.555  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.434  -2.309   3.173  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.769  -0.477   1.037  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.949  -0.991   1.521  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.298  -2.167   0.788  0.00  0.00           C+0
HETATM   26  H   UNK     0       6.486   2.247  -0.036  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.629   0.584   0.533  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.526   1.749   1.361  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.610   1.722  -1.272  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.601   3.106  -0.586  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.365   3.904  -2.131  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.643   1.262  -2.571  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.028  -0.970  -2.401  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.799  -1.644  -1.142  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.395  -0.780   1.436  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.694  -3.020   3.963  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.788  -2.829   2.459  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.912  -1.468   3.642  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.555  -2.960   0.922  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.430  -1.946  -0.278  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.253  -2.531   1.177  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3   23    4    2                                                  
CONECT    4    3    5   29                                                  
CONECT    5   19    4    6                                                  
CONECT    6    5    7   18                                                  
CONECT    7    8    6   30                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11    8   17                                                  
CONECT   11   13   10   12                                                  
CONECT   12   11   31                                                       
CONECT   13   14   11   32                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   33                                                       
CONECT   16   14   17   34                                                  
CONECT   17   16   18   10                                                  
CONECT   18   17    6                                                       
CONECT   19    5   20   35                                                  
CONECT   20   19   23   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   36   37   38                                             
CONECT   23   20    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   39   40   41                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    7                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   19                                                            
CONECT   36   22                                                            
CONECT   37   22                                                            
CONECT   38   22                                                            
CONECT   39   25                                                            
CONECT   40   25                                                            
CONECT   41   25                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    5.9276    1.4120    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055    1.0498   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5163    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.9897   -0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482    0.5333    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    1.0302   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1369    2.3322   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    2.7623   -1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    3.9391   -1.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    1.7211   -1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7237    2.0230   -1.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    3.2947   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.0102   -2.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3022   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974   -1.3270   -2.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -0.6141   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    0.4041   -1.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    0.0421   -0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.4329    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.9393    1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8855    2.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -2.3088    3.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -0.4769    1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488   -0.9913    1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -2.1666    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4858    2.2471   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6293    0.5841    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260    1.7485    1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    1.7224   -1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007    3.1062   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    3.9037   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6432    1.2620   -2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0281   -0.9697   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7993   -1.6444   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.7803    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6943   -3.0200    3.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.8286    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -1.4679    3.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546   -2.9598    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297   -1.9455   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2533   -2.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
  5 19  1  0
 14 16  1  0
 19 20  2  0
 13 11  1  0
 20 23  1  0
 11 10  2  0
 23  3  2  0
 17 16  2  0
  3  4  1  0
  4  5  2  0
  6  5  1  0
 17 18  1  0
 23 24  1  0
 10  8  1  0
 24 25  1  0
  8  7  1  0
 14 15  1  0
  7  6  2  0
 11 12  1  0
  6 18  1  0
  3  2  1  0
 17 10  1  0
 20 21  1  0
  8  9  2  0
  2  1  1  0
 21 22  1  0
 13 32  1  0
 16 34  1  0
  7 30  1  0
 19 35  1  0
  4 29  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
 15 33  1  0
 12 31  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one	ChEBI
Tricetin 3',4',5'-trimethyl ether	ChEBI
5, 7-Dihydroxy-3',4',5'-trimethoxyflavone	HMDB
5,7-Dihydroxy-3',4',5'-trimethoxy flavone	HMDB
5,7-Dihydroxy-3',4',5'-trimethoxy-flavone	HMDB
5,7-Dihydroxy-3',4',5'-trimethoxyflavon	HMDB
Dimethyl benzoylphosphonate	HMDB
Flavone, 5,7-dihydroxy-3',4',5'-trimethoxy- (8ci)	HMDB
5,7-Dihydroxy-3',4',5'-trimethoxyflavone	ChEBI

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3154 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

5,7-dihydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

Traditional Name

3',4',5'-O-trimethyltricetin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C([H])=C(OC2=C1[H])C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C18H16O7/c1-22-15-4-9(5-16(23-2)18(15)24-3)13-8-12(21)17-11(20)6-10(19)7-14(17)25-13/h4-8,19-20H,1-3H3

InChI Key

CPCPHNWWTJLXKQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Asarina procumbens	KNApSAcK Database	22123792
Bridelia ferruginea	KNApSAcK Database	22123792
Bromus pauciflora	KNApSAcK Database	22123792
Chrysanthemum morifolium	LOTUS Database	35616633
Haplopteris anguste-elongata	LOTUS Database	35616633
Hordeum vulgare hexastichon	KNApSAcK Database	22123792
Lycopodium japonicum	LOTUS Database	35616633
Nonea pulla	KNApSAcK Database	22123792
Teucrium heterophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.92	ALOGPS
logP	2.54	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	34.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037692

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5379265

PDB ID

Not Available

ChEBI ID

543745

Good Scents ID

rw1504821

References

General References

Ahmed SA, Kamel EM: Cytotoxic activities of flavonoids from Centaurea scoparia. ScientificWorldJournal. 2014;2014:274207. doi: 10.1155/2014/274207. Epub 2014 Jun 11. [PubMed:25114960 ]
Wang QH, Ao WL, Wang XL, Bao XH, Wang JH: Two new flavonoid glycosides from Artemisia frigida Willd. J Asian Nat Prod Res. 2010 Nov;12(11):950-4. doi: 10.1080/10286020.2010.510469. [PubMed:21061216 ]
Wu PL, Hsu YL, Zao CW, Damu AG, Wu TS: Constituents of Vittaria anguste-elongata and their biological activities. J Nat Prod. 2005 Aug;68(8):1180-4. doi: 10.1021/np050060o. [PubMed:16124757 ]
Park, Y., et al. (2007). Park, Y., et al, Magn. Reson. Chem. 45, 1072 (2007). Mag. Reson. Chem..

Showing NP-Card for 5,7-dihydroxy-3',4',5'-trimethoxyflavone (NP0024993)

MOL for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

3D MOL for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

3D SDF for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

3D-SDF for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

PDB for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

3D PDB for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

SMILES for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

INCHI for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

Structure for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)

3D Structure for NP0024993 (5,7-dihydroxy-3',4',5'-trimethoxyflavone)